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Director Sydney Pollack had a special relationship with star Robert Redford,
whom he directed in seven films including Out of Africa, The Way We Were, and Three Days of the Condor. Redford spoke to TIME about his old friend, who
died Monday of cancer at the age of 73.

How long did you know each other?

I've known him for 48 years, almost half a century. We met on a film in
1960. It was a low-budget black-and-white independent film called War Hunt.
He was an actor. I was an actor. It was the first film I ever acted in. He
and I became friends on that film and we became I would say kindred spirits.
Like any novice artists starting out, we decided that we knew everything
that was wrong about the production. We commiserated on it and we kind of
bonded on that. We had very similar sensibilities and I think very similar
ambitions to do special work, or at least what we thought was special.

What was it about him that allowed you to work together so well so often?

Because of where he was from, South Bend, Indiana, Sydney had a
real love of pop culture and pop celebrity, but he was smart enough to mask
that with more abstract ways of thinking. He had a very strong sense of
commerciality, and that's why he always worked with stars. I think he grew up
in a community where stars where very important. He used to tell me, "I
went to the movies to see people like Natalie Wood and Judy Garland." He was
taken with that part of the business and I think he wanted to be part of
that business, but he was smart enough to know that he could sort of cover
that with a more offbeat intellectual style, and I think that was his great
gift  to cover what could have been just sort of crass commercial
filmmaking with a whole artistic [approach] that was more abstracted and was more
hip and was more offbeat. So I think Sydney's ability to connect the more
commercial strain with the more abstract was a special gift.

Much like you, Sydney was an actor, director, and producer. Did he enjoy
tackling all those roles?

I think he always had it on his mind he would like to be a producer. I
think that in his later years, he went in that direction because perhaps
he got more tired of directing. I think that the best times that he
and I had were when the film industry was a different
business. It was mainly because, in more of the films he and I did during the
time we worked together, we were going against the grain. The business has so drastically
changed now, it's just a completely different business than it was. And I
don't know that we could ever produce the fun he and I had during the '60s, '70s and '80s, when we were constantly trying to forge projects
that were going to be hard to get the studios to go with and
working against those odds. A lot of the appeal was it was great fun. Success I think kind of changed that.

I think when success comes, something else enters the picture. There's a
new kind of pressure that enters the picture and you're no longer in the
position you were when you were working uphill and so much against the
grain. I think around the time that came, Sydney became more interested in
being in total control and being more of a producer. I think that's sort of
where he went. And I went in a slightly different direction. I went more in
the world of independent films. But we still stayed close and our families
grew up together. We shared a lot of time together.

Even as a producer, he did big movies with Anthony Minghella like The
Talented Mr. Ripley and Cold Mountain. Did you ever try to get him to go the more
independent route?

I think Sydney's heart was more in those [commercial] films. His track
record shows that his instinct was always to go to with stars and large
films. And at one point, I said, "Why don't we just get a handheld and go
out and do a little black-and-white?" I just don't think he was that
interested in that. I think he was interested in larger scale films.

Did y'all ever talk in later years about how far you had come from that
first movie in 1960?

When I would go to see him these last months, I just remember telling him  because I didn't know what was going to stick or not  I said, "You know
Sydney, the most fun I had was in those years, when we were doing original
pieces and not adaptations and not remakes or anything like that"  when we
were doing original pieces about something, and it was fun because it was
always going slightly uphill, and you're always fighting against whatever
obstacles there were. When I look back on it I realize how much fun it was.
I said, I don't know about you, but success is a funny
game. I don't know that the most fun wasn't when you were striving toward
it, rather than achieving it.